Additive-Controlled Divergent Synthesis of Tetrasubstituted 1,3-Enynes and Alkynylated 3<i>H</i>-Pyrrolo[1,2-<i>a</i>]indol-3-ones via Rhodium Catalysis
Fei Zhao, Xin Gong, Yangbin Lu, Qiao Jin, Xiuwen Jia, Hangcheng Ni, Xiaowei Wu, Xiaoning Zhang
Abstract
Herein, we report the additive-controlled divergent synthesis of tetrasubstituted 1,3-enynes and alkynylated 3H-pyrrolo[1,2-a]indol-3-ones through rhodium-catalyzed C–H alkenylation/DG migration and [3+2] annulation, respectively. This protocol features rare directing group migration in 1,3-diyne-involved C–H activation, excellent regio- and stereoselectivity, excellent monofunctionalization over difunctionalization, broad substrate scope, moderate to high yields, good functional group compatibility, and mild redox-neutral conditions.
Topics & Concepts
ChemistryAnnulationRhodiumCatalysisCombinatorial chemistryStereoselectivityFunctional groupSubstrate (aquarium)Reaction conditionsStereochemistryMedicinal chemistryOrganic chemistryOceanographyPolymerGeologyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques